US4080362A - Organotin stabilizers - Google Patents

Organotin stabilizers Download PDF

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Publication number
US4080362A
US4080362A US05/613,434 US61343475A US4080362A US 4080362 A US4080362 A US 4080362A US 61343475 A US61343475 A US 61343475A US 4080362 A US4080362 A US 4080362A
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US
United States
Prior art keywords
alkyl
organotin
sub
formula
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US05/613,434
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English (en)
Inventor
Ronald E. Hutton
Vincent Oakes
Joseph Burley
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Akzo NV
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Akzo NV
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Publication date
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Priority to US05/793,363 priority Critical patent/US4105684A/en
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Publication of US4080362A publication Critical patent/US4080362A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/22—Tin compounds
    • C07F7/226—Compounds with one or more Sn-S linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/22—Tin compounds
    • C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen

Definitions

  • This invention relates to the preparation of certain new organotin trihalides, which are particularly useful for conversion into organotin stabilizers for polyvinyl chloride or other polymers.
  • organotin compounds In the synthesis of organotin compounds the formation of a tin-carbon bond constitutes a necessary step.
  • a known method of forming such a bond is the Grignard route by the reaction
  • R alkyl or substituted alkyl.
  • a different method is the aluminum alkyl route by the reaction 3 SnCl 4 + 4 R 3 Al ⁇ 3 R 4 Sn + 4 AlCl 3 .
  • a third method is the Wurtz route:
  • the R 4 Sn obtained may serve as a starting material for the preparation of RSnHal 3 , R 2 SnHal 2 and R 3 SnHal, where Hal represents a halogen atom.
  • Hal represents a halogen atom.
  • R 1 , R 2 , R 3 , and R 4 represent an alkyl group, with 1- 18 carbon atoms an oxygen-containing hydrocarbon group or a hydrogen atom, provided that at least one of these groups contains a carbonyl group adjacent to the carbon-carbon double bond, after which the reaction product with the formula ##STR3## is isolated from the medium.
  • the halide may be chloride, bromide, iodide or even fluoride, although for reasons of cost and optimum yield chloride is usually preferred.
  • the olefin be activated, that is at least one of R 1 , R 2 , R 3 or R 4 contains an activating carbonyl radical adjacent to the olefinic double bond.
  • the activating carbonyl radical may be an acid group, an ester group, an aldehyde group, an acid halide, or a ketone group.
  • olefins suitable to be used in the process according to the invention are:
  • the starting materials react with each other at ambient temperature (10° - 30° C.) to form the desired compound in a polar solvent, which is preferably an alkyl ether such as a diethyl ether.
  • a polar solvent which is preferably an alkyl ether such as a diethyl ether.
  • the new organotin compounds prepared according to the invention may be converted into very useful organotin stabilizers for polyvinyl chloride and other polymers by any of the established techniques for stabilizer preparation.
  • Such preparation usually involves reaction with organic fatty acids having 6 to 18 carbon atoms, partial esters of maleic acid, alkyl thiols or mercapto-esters.
  • organotin trihalides prepared according to the invention have a certain stabilizing effect themselves on polymers and may also find utility as catalysts in the preparation of polyurethane foam and silicone resins or in esterification reactions.
  • This compound (I) was shown to give heat stability in rigid polyvinyl chloride polymer comparable to that obtained by the commonly used monobutyltin tris(isooctylthioglycollate).
  • compound I was satisfactorily substituted for conventional dibutyltin bis(iso octylthioglycollate) in the production of P.V.C. bottles, at a level of 1%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US05/613,434 1974-09-16 1975-09-15 Organotin stabilizers Expired - Lifetime US4080362A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US05/793,363 US4105684A (en) 1974-09-16 1977-05-03 Process for the preparation of organotin trihalides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL7412230A NL7412230A (nl) 1974-09-16 1974-09-16 Werkwijze voor de bereiding van organotintri- halogeniden.
NL7412230 1974-09-16

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US05/793,363 Division US4105684A (en) 1974-09-16 1977-05-03 Process for the preparation of organotin trihalides

Publications (1)

Publication Number Publication Date
US4080362A true US4080362A (en) 1978-03-21

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
US05/613,434 Expired - Lifetime US4080362A (en) 1974-09-16 1975-09-15 Organotin stabilizers

Country Status (6)

Country Link
US (1) US4080362A (enrdf_load_stackoverflow)
JP (2) JPS604197B2 (enrdf_load_stackoverflow)
DE (1) DE2540210C3 (enrdf_load_stackoverflow)
FR (1) FR2285392A1 (enrdf_load_stackoverflow)
GB (1) GB1487879A (enrdf_load_stackoverflow)
NL (1) NL7412230A (enrdf_load_stackoverflow)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4158669A (en) * 1977-05-06 1979-06-19 Ciba-Geigy Corporation Organo-tin compounds
US4167520A (en) * 1976-01-23 1979-09-11 Akzo N.V. Process for preparing organotin trihalides
US4188334A (en) * 1977-09-09 1980-02-12 Ciba-Geigy Corporation Organotin compounds
US4196137A (en) * 1977-05-06 1980-04-01 Ciba-Geigy Corporation Process for the production of organo-tin compounds
US4202830A (en) * 1977-08-09 1980-05-13 Hoechst Aktiengesellschaft Organotin halides
US4237043A (en) * 1977-08-09 1980-12-02 Hoechst Aktiengesellschaft Organotin compounds, the preparation and use thereof
US4244746A (en) * 1979-07-16 1981-01-13 Conoco, Inc. Single package additive for thermoplastic formulation
US4329279A (en) * 1979-05-23 1982-05-11 Societe Nationale Elf Aquitaine Organostannic stabilizing compositions for vinyl halide resins
US4795820A (en) * 1985-09-25 1989-01-03 Politchnika Warszawska Method of manufacturing tinorganic compounds and stabilizers
EP1743898A1 (en) 2005-07-12 2007-01-17 Arkema Vlissingen B.V. Process for the preparation of monoalkyl tin trihalides and dialkyl tin dihalides
CN108585783A (zh) * 2018-06-29 2018-09-28 陈雨 一种环保节能砖

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1552774A (en) * 1975-11-25 1979-09-19 Akzo Nv Organotin stabilizer compositions and polyvinyl resins stabilized therewith
GB1541503A (en) * 1976-01-23 1979-03-07 Akzo Nv Process for the preparation of organotin compounds
JPS52152446A (en) * 1976-06-14 1977-12-17 Adeka Argus Chem Co Ltd Rubber-modified styrene resin compositions
JPS535127A (en) * 1976-07-05 1978-01-18 Nitto Kasei Kk Preparation of organotin trihalides having functional group
EP0002019A1 (de) * 1977-11-14 1979-05-30 Ciba-Geigy Ag Verfahren zur Herstellung von Organozinnverbindungen
DE2850150A1 (de) * 1978-11-18 1980-05-29 Hoechst Ag Verfahren zur herstellung von organozinntrihalogeniden und ihre verwendung
FR2458554A1 (fr) * 1979-05-23 1981-01-02 Elf Aquitaine Procede de preparation de trihalogenures organostanniques
JPS6256699U (enrdf_load_stackoverflow) * 1985-09-30 1987-04-08

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2731482A (en) * 1950-10-05 1956-01-17 Firestone Tire & Rubber Co Organotin trimercaptides
US3607893A (en) * 1968-12-18 1971-09-21 M & T Chemicals Inc Addition of trihalostannous acid to olefins
US3657294A (en) * 1970-03-16 1972-04-18 M & T Chemicals Inc Process for preparing organotin mercaptides
US3705919A (en) * 1965-08-13 1972-12-12 Hercules Inc Reactions of organo-metallic compounds of platinum and palladium group viii metals with ethylenically unsaturated compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2731482A (en) * 1950-10-05 1956-01-17 Firestone Tire & Rubber Co Organotin trimercaptides
US3705919A (en) * 1965-08-13 1972-12-12 Hercules Inc Reactions of organo-metallic compounds of platinum and palladium group viii metals with ethylenically unsaturated compounds
US3607893A (en) * 1968-12-18 1971-09-21 M & T Chemicals Inc Addition of trihalostannous acid to olefins
US3657294A (en) * 1970-03-16 1972-04-18 M & T Chemicals Inc Process for preparing organotin mercaptides

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
J. Organometallic Chemistry, 25 101-109 (1970). *
Kagaku (Kyoto) 26 137-141 (1971). *
Sawyer, Organotin Compounds, Marcel Dekker, Inc., N.Y., vol. 2, pp. 261, 374, 375, 410, 411 (1971). *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4167520A (en) * 1976-01-23 1979-09-11 Akzo N.V. Process for preparing organotin trihalides
US4196137A (en) * 1977-05-06 1980-04-01 Ciba-Geigy Corporation Process for the production of organo-tin compounds
US4158669A (en) * 1977-05-06 1979-06-19 Ciba-Geigy Corporation Organo-tin compounds
US4202830A (en) * 1977-08-09 1980-05-13 Hoechst Aktiengesellschaft Organotin halides
US4237043A (en) * 1977-08-09 1980-12-02 Hoechst Aktiengesellschaft Organotin compounds, the preparation and use thereof
US4188334A (en) * 1977-09-09 1980-02-12 Ciba-Geigy Corporation Organotin compounds
US4329279A (en) * 1979-05-23 1982-05-11 Societe Nationale Elf Aquitaine Organostannic stabilizing compositions for vinyl halide resins
US4244746A (en) * 1979-07-16 1981-01-13 Conoco, Inc. Single package additive for thermoplastic formulation
US4795820A (en) * 1985-09-25 1989-01-03 Politchnika Warszawska Method of manufacturing tinorganic compounds and stabilizers
EP1743898A1 (en) 2005-07-12 2007-01-17 Arkema Vlissingen B.V. Process for the preparation of monoalkyl tin trihalides and dialkyl tin dihalides
US20090131704A1 (en) * 2005-07-12 2009-05-21 Arkema Vlissingen Process for the Preparation of Monoalkyltin Trihalides and Dialkyltin Dihalides
US7592472B2 (en) 2005-07-12 2009-09-22 Arkema Vlissingen Process for the preparation of monoalkyltin trihalides and dialkyltin dihalides
EP2325192A1 (en) 2005-07-12 2011-05-25 Arkema Vlissingen Process for the preparation of dialkyltin dihalides
CN108585783A (zh) * 2018-06-29 2018-09-28 陈雨 一种环保节能砖

Also Published As

Publication number Publication date
JPS6035038A (ja) 1985-02-22
FR2285392B1 (enrdf_load_stackoverflow) 1979-07-13
JPS6234787B2 (enrdf_load_stackoverflow) 1987-07-29
JPS5152138A (enrdf_load_stackoverflow) 1976-05-08
GB1487879A (en) 1977-10-05
JPS604197B2 (ja) 1985-02-01
NL7412230A (nl) 1976-03-18
DE2540210C3 (de) 1983-12-01
FR2285392A1 (fr) 1976-04-16
DE2540210B2 (de) 1979-04-05
DE2540210A1 (de) 1976-03-25

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